Palwinder Singh, Anu Mittal, P. Kaur
Feb 6, 2006
Citations
0
Influential Citations
9
Citations
Journal
Tetrahedron
Abstract
Abstract 2-Oxoglutaric acid ( 1 ) underwent facile indium mediated allylation with allyl bromide ( 2 ), and ethyl 4-bromocrotonate ( 3 ), cinnamyl bromide ( 4 ) and subsequent in situ dehydration to provide respective 5-oxotetrahydrofuran-2-carboxylic acids 5–7 (90–95%). The reaction of 1 with 3 and 4 proceeded with high regio and stereo selectivity to provide only γ-addition products with syn stereochemistry as ascertained from their cyclic products. Compounds 5–7 underwent diastereoselective iodocyclization to provide respective 1,7-dioxa-2,6-dioxospiro[4.4]nonanes 8–13 . The relative stereochemistries have been ascertained by single crystal X-ray structures, NOE experiments and coupling constants in 1H NMR spectra.